It’s been more than a hot minute since I posted something. The last post was all about the adventure at Unbound Gravel which was more than two months ago. At that time, the plan was to write something about my time in Colorado which included hiking in Rocky Mountain National Park, gravel riding in Boulder, and the drive back to Wisconsin. (The Instagram feed has all the pretty pictures and a good enough summary.) Sounded like a great plan at the time. Little did I know how life was going to change in all sorts of ways and to this day I am still processing it. I started a new job, went on various adventures, attended things I never imagined, tried my hand at dating in my mid-to-late 30s —all things that I never had on my agenda June 1.

Stepping into chaos and the unknown at work

The first day back from Colorado, I opened my email to find that I had a job interview (internal) that same day for a position I applied weeks ago. At first, I got an email from Workday saying my application was declined, but then I had a calendar invite with the hiring manager. Confusion and panic set in. I quick ran home to change and do the interview over Zoom. 

The position I applied for was for a digital product manager position in NM’s digital product and design department specifically focusing on disability claims (where I worked). The position basically works with our software engineering team and the business (DI claims) to develop digital tools. The PM is the big picture guy. It was the type of job that I had on my five-year plan. I took a quick look at the hiring manager to see what her background was, and, of course, her employee profile was blank. I did a quick look at LinkedIn and saw that she seemed like kind of a big deal and did a lot of big things. No pressure, right?

I logged into the call and find one of the PMs that I worked with on various projects in the past. He started explaining why my background and experience would be a good fit. The manager then gets on, and we talk about random things. Then she starts talking about her plans for me and the position and then after about 15 minutes asks me the first question about why I wanted the position. I don’t exactly what I said, but I saw the excitement in her face. She then asks me about what my favorite product was. Kind of a strange question (which she admitted was strange to her when asked many years ago). Dumbfounded, I went on to explain my Tarmac SL7 that I bought earlier in the year and spewed a line of BS about it. The PM then went out to sing my praises and then we ended the call. 

The next business day I get calendar invite for a chat with the senior director of the product space I would be working in, but it wasn’t an interview. It was labeled “touch base” and it was later in the week. The morning of that meeting, I ran into my current senior director, and we chatted about my interview, how it went, etc., and I could tell something was up. She was talking in the past tense and talked about how much she’s going to miss me, but it would be a big win for the department in my new job. 

The morning calm in the chaos of the hiring process.

Later that day, I had the Zoom call with the product senior director, and he was talking like I was hired. It was more of a get-to-know you chat. I could tell this is a guy I would like to work for. The half hour zoomed on by and I felt confident that I would changing jobs. 

The next day, I had to log into Workday to correct some PTO entries and I went to my job application to see if there was anything there just to fulfill my curiosity. It was listed as “pre-hire qualification.” I was thinking what the hell does that mean? My current boss at the time (who was in her first week as my manager) told me I would be taken out of the new claim rotation later that day. It was still crickets from HR. 

Finally, I get a slack message the following Monday from the hiring manager asking she could call me with a smiley face. I knew this was it. I got the job. She gave me the offer which included a significant pay increase and a start date of 7/18 but explained that wanted me to start sooner, but of course company protocol. She explained that she first talked to my current senior director Friday but was told she also had to talk to my current manager which was done that morning. Because big companies have protocols to follow, naturally. Of course, I accepted the position without much thought or care of what I was going to get myself into. 

My start date was 7/18 with a two-week transition to 8/1. I had a little over a month to get my claim work cleaned out before I started and two weeks to wrap up loose ends. Turns out not everyone in my old department was happy with me leaving. There was a lot of attrition in the department for quite some time. It was mostly due to retirements, newer people that couldn’t cut it and people that were generally dissatisfied with how things were going. I was neither of them, but people kept saying it felt like I was “jumping off a sinking ship.” I reiterated that this was my dream job when I started with NM, but it didn’t matter. I was a traitor. 

My days slowly grew less and less busy. I still didn’t have an idea of what all my new job entitled, but that wasn’t my focus. My soon-to-be-boss (the boss lady I as call her), set up a bunch of lunches and invited me to a team meeting to introduce myself to the team. The team meeting was nice to get to know everyone and to get an idea of what the dynamics were and who did what. During that first meeting I could tell there was some tension in the new team. Great first impression.

Product managers are the big picture people and business analysts take those big ideas and create the “stories” or the work that engineers develop. Typically, someone with my background would start as a BA then move to a PM if they so desired as the likely career path from the business. So already jumped the line there. The next day I got to pick out my desk (first time in six years I got to do that) and talked to the boss lady about the first week of the job. She told me not to worry about it, and I’ll be fine. Sure, I thought.

Week 1 on the job consisted of getting thrown into PI (Program Increment) planning, and meetings for new projects that the boss lady wanted me involved in; if only just to observe and listen. I felt I was being pulled in a million different directions. I mean, what else was I going to do? I didn’t know any better. 

Every morning I had at minimum 30 minutes of peace on the bike commute despite what the day would bring.

Then the first of many bombshells went off. During a lunch with just the boss, she told me she had to have me even before I interviewed and before I had stepped foot back in Wisconsin. She told me I was a unicorn (a frequent term she’s used with me around the team), and it would have been crazy not to poach me. I mean, how can you respond to that? No one has ever said that to me in my career.

After the first week, I could sense that I was entering a team that was undergoing substantial changes on how they operated. I also could sense that the boss lady was assembling a team of people that she wanted, not a team that she was inheriting. Week two seemed to solidify this theory of mine. Meeting after meeting, I could see how certain people would talk about what they were doing (making it sound more important or substantial) and go into self-preservation mode when defending what they did. I could see the tension in the air when discussing how we are going to do our work. Since I didn’t know any better, I kept my mouth shut, but took mental notes as navigating this tension could be life or death when it comes to my success and my sanity. 

I still had some reservations about getting up to speed and whether there was going to be any formalized training or onboarding, so I reached out to the boss to find out and to answer those questions and concerns that I had. Turns out, I had nothing to worry about. She reiterated that I was exceeding all expectations, received a lot of positive feedback and that it will click eventually. A bit of a sigh of relief there. But then she went on to explain another bombshell. Her plan for me is to take on the lead PM role when the current one retires. No pressure two weeks in, right? 

So far, the new job has had its ups and downs, and has felt like riding one giant roller coaster. Every day I learn something new. I keep being told that I am exceeding all expectations, but I still feel like I’m not contributing to anything. I guess at this point, it is all natural to have all these conflicting feelings. I have found that for the first time in my adult life, I can trust my boss completely and she trusts me as well based on various private conversations this week. It’s a really strange feeling.

What’s next in part II?

Since starting the new gig, my days have been waking up, going to work, ride the bike after work and go to bed. And repeat.  But there have been a few other stories to be told including memorable bike rides, triathlons, and my attempt at dating in my late-30s.